What is the cheapest airline that flies from Wisconsin to Caribbean Islands?

Spirit Airlines, Arajet, and American Airlines are the most popular carriers operating from Wisconsin to Caribbean Islands

What airlines fly to Caribbean Islands?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Wisconsin according to our data. American Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

How long is the flight from Wisconsin to Caribbean Islands?

The flight from Wisconsin to Caribbean Islands depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Milwaukee (a popular airport in Wisconsin) to Incheon Intl Airport (the most popular airport in Caribbean Islands), then the flight time is 16h 47m on average. If you fly from Madison (another popular airport in Wisconsin) to Incheon Intl Airport, then the average flight time is 17h 46m.

How many flights depart from Wisconsin to Caribbean Islands on average per week?

As of July 2025, 83 flights take off from Wisconsin and land in Caribbean Islands each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

Prices for flights from Wisconsin to Caribbean Islands refresh daily.

How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

As of July 2025, there are 11 operators available to choose from for flights from Wisconsin to Caribbean Islands.

How old do you have to be to fly from Wisconsin to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$91 Cheap Flights from Wisconsin to Caribbean Islands in 2025

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Find the cheapest flights from Wisconsin to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:23 pm - 12:06 amORD-SJU

4h 43mnonstop

10:16 pm - 9:22 amSJU-ORD

12h 06m1 stop

$189Spirit Airlines

Find Deal

Mon, Aug 11 - Fri, Aug 15

12:55 pm - 6:34 pmORD-SJU

4h 39mnonstop

7:40 pm - 11:56 pmSJU-ORD

5h 16mnonstop

$190Spirit Airlines

Find Deal

Thu, Sep 25 - Mon, Sep 29

11:28 am - 2:39 amORD-SJU

14h 11m1 stop

10:16 pm - 9:22 amSJU-ORD

12h 06m1 stop

$214

Find Deal

Tue, Aug 12 - Fri, Aug 15

3:00 pm - 10:45 pmMKE-SJU

6h 45m1 stop

3:05 pm - 9:50 pmSJU-MKE

7h 45m1 stop

$215Southwest

Find Deal

Tue, Sep 16 - Tue, Sep 23

12:55 pm - 6:40 pmORD-SJU

4h 45mnonstop

3:21 pm - 11:33 pmSJU-ORD

9h 12m1 stop

$219

Find Deal

Mon, Aug 25 - Sat, Aug 30

6:23 pm - 12:47 pmMKE-SJU

17h 24m2 stops

4:45 pm - 10:04 amSJU-MKE

18h 19m2 stops

$220American Airlines

Find Deal

Sun, Sep 21 - Sat, Sep 27

7:00 am - 4:51 pmMKE-SJU

7h 51m1 stop

2:12 pm - 8:12 pmSJU-MKE

8h 00m1 stop

$225Delta

Find Deal

Wed, Jan 21 - Thu, Jan 29

1:20 pm - 11:05 pmMKE-SJU

8h 45m1 stop

7:10 am - 12:11 amSJU-MKE

18h 01m1 stop

$240American Airlines

Find Deal

Sat, Oct 11 - Thu, Oct 16

3:00 pm - 10:45 pmMKE-SJU

6h 45m1 stop

1:35 pm - 10:05 pmSJU-MKE

9h 30m2 stops

$265Southwest

Find Deal

Tue, Sep 16 - Tue, Sep 23

7:00 am - 5:10 pmMKE-SJU

8h 10m1 stop

2:26 pm - 8:07 pmSJU-MKE

7h 41m1 stop

$293Delta

Find Deal

Tue, Nov 11 - Thu, Nov 27

Southwest flights from Wisconsin to Caribbean Islands

Our best Southwest deals on Wisconsin to Caribbean Islands flight tickets

Southwest

Sep 16

MKE3:00 pmMilwaukee-Mitchell

6h 45m

1 stop

SJU10:45 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU3:05 pmSan Juan Luis Munoz Marin Intl

7h 45m

1 stop

MKE9:50 pmMilwaukee-Mitchell

$215

Find similar

Southwest

Sep 16

MKE3:00 pmMilwaukee-Mitchell

6h 45m

1 stop

SJU10:45 pmSan Juan Luis Munoz Marin Intl

Sep 23

SJU1:35 pmSan Juan Luis Munoz Marin Intl

9h 30m

2 stops

MKE10:05 pmMilwaukee-Mitchell

$265

Find similar

Southwest

Nov 17

ORD6:05 amChicago O'Hare Intl

5h 10m

1 stop

NAS12:15 pmNassau Intl

Nov 21

NAS1:10 pmNassau Intl

9h 40m

1 stop

ORD9:50 pmChicago O'Hare Intl

$447

Find similar

Spirit Airlines flights from Wisconsin to Caribbean Islands

Our best Spirit Airlines deals on Wisconsin to Caribbean Islands flight tickets

Spirit Airlines

Aug 11

ORD6:23 pmChicago O'Hare Intl

4h 43m

SJU12:06 amSan Juan Luis Munoz Marin Intl

Aug 15

SJU10:16 pmSan Juan Luis Munoz Marin Intl

12h 06m

1 stop

ORD9:22 amChicago O'Hare Intl

$189

Find similar

Spirit Airlines

Sep 25

ORD12:55 pmChicago O'Hare Intl

4h 39m

SJU6:34 pmSan Juan Luis Munoz Marin Intl

Sep 29

SJU7:40 pmSan Juan Luis Munoz Marin Intl

5h 16m

ORD11:56 pmChicago O'Hare Intl

$190

Find similar

Spirit Airlines

Nov 6

ORD6:55 amChicago O'Hare Intl

4h 38m

SJU1:33 pmSan Juan Luis Munoz Marin Intl

Nov 13

SJU2:38 pmSan Juan Luis Munoz Marin Intl

5h 22m

ORD6:00 pmChicago O'Hare Intl

$191

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/11

6:23 pm-12:06 am

Nonstop4h 43m

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

$189

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 9/25

12:55 pm-6:34 pm

Nonstop4h 39m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:40 pm-11:56 pm

Nonstop5h 16m

$190

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/12

11:28 am-2:39 am

1 stop14h 11m

San Juan Luis Munoz Marin Intl

Fri 8/15

10:16 pm-9:22 am

1 stop12h 06m

$214

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

3:00 pm-10:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Tue 9/23

3:05 pm-9:50 pm

1 stop7h 45m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/25

12:55 pm-6:40 pm

Nonstop4h 45m

San Juan Luis Munoz Marin Intl

Sat 8/30

3:21 pm-11:33 pm

1 stop9h 12m

$219

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/21

6:23 pm-12:47 pm

2 stops17h 24m

San Juan Luis Munoz Marin Intl

Sat 9/27

4:45 pm-10:04 am

2 stops18h 19m

$220

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 1/21

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:12 pm-8:12 pm

1 stop8h 00m

$225

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 10/11

1:20 pm-11:05 pm

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Thu 10/16

7:10 am-12:11 am

1 stop18h 01m

$240

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

3:00 pm-10:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Tue 9/23

1:35 pm-10:05 pm

2 stops9h 30m

$265

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 11/11

7:00 am-5:10 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Thu 11/27

2:26 pm-8:07 pm

1 stop7h 41m

$293

Flights are sorted by cheapest round-trip flights first.

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How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $325. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $356.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Wisconsin to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $477. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Wisconsin to Caribbean Islands in the evening for as low as $360. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $458. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $435 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Wisconsin for as low as $351 on momondo.

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There are 1 cabin classes available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Best Price Found	$91
Fastest flight time	3h 18m
Direct flights	Every day
Airports in Caribbean Islands	6 airports

The best one-way flight to Caribbean Islands from Wisconsin in the past 72 hours is $91. The best round-trip flight deal from Wisconsin to Caribbean Islands found on momondo in the last 72 hours is $189.

The fastest flight from Wisconsin to Caribbean Islands takes 3h 18m

Direct flights go from Wisconsin to Caribbean Islands every day.

There are 6 airports near Caribbean Islands: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

Search flight deals

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?
Prices for flights from Wisconsin to Caribbean Islands refresh daily.
How many operators does momondo search for flights from Wisconsin to Caribbean Islands?
As of July 2025, there are 11 operators available to choose from for flights from Wisconsin to Caribbean Islands.
How old do you have to be to fly from Wisconsin to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Wisconsin to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Wisconsin to Caribbean Islands is Airbus A320-100/200 (19.01% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (9.85%), Boeing 737-800 Passenger/BBJ2 (winglets) (8.50%), and Boeing 737-700 Passenger/BBJ1 (winglets) (7.45%).

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $129	Free Cancellation	Rating 5.9 3,239 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $208	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $215	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Delta	PriceFrom $225	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $269	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $325	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
Sun Country Air	PriceFrom $519	Free Cancellation	Rating 6.9 334 reviews	Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Wisconsin to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

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Cheap flights from Wisconsin to Caribbean Islands from $91

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Caribbean Islands departing on 8/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Wisconsin to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Southwest flights from Wisconsin to Caribbean Islands

Our best Southwest deals on Wisconsin to Caribbean Islands flight tickets

Spirit Airlines flights from Wisconsin to Caribbean Islands

Our best Spirit Airlines deals on Wisconsin to Caribbean Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $325. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $356.

What is the cheapest day to depart on your flight to Caribbean Islands?

What is the cheapest time of day to depart on your flight to Caribbean Islands?

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There are 1 cabin classes available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

What is the cheapest airline that flies from Wisconsin to Caribbean Islands?

Spirit Airlines, Arajet, and American Airlines are the most popular carriers operating from Wisconsin to Caribbean Islands

What airlines fly to Caribbean Islands?

How many flights depart from Wisconsin to Caribbean Islands on average per week?

As of July 2025, 83 flights take off from Wisconsin and land in Caribbean Islands each week. The most common flight departure day for this route is Thu, with 16% of weekly flights taking off on this day.

How long is the flight from Wisconsin to Caribbean Islands?

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Best Price Found

Fastest flight time

Direct flights

Airports in Caribbean Islands

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

How old do you have to be to fly from Wisconsin to Caribbean Islands?

What documentation or ID do you need to fly to Caribbean Islands?

What is the most popular plane model from Wisconsin to Caribbean Islands?

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

How can momondo help me find flights from Wisconsin to Caribbean Islands?

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo